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Pendry Chicago

Downtown Chicago

€456

per person

20 Nov - 25 Nov

just found

Return flight included

Boston (BOS) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on 7 Oct 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

€1,050

per person

20 Nov - 25 Nov

just found

Return flight included

Boston (BOS) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on 6 Oct 2025

Swissotel - Chicago

Downtown Chicago

€694

per person

10 Nov - 16 Nov

found 1 day ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on 9 Oct 2025

Tours & day trips

See all 157 activities

Architecture River Tour

Free cancellation available

Private & custom tours

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Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Ping Tom Memorial Park

After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

South Wentworth Street

You can find the perfect gifts to bring home at South Wentworth Street during your trip to Chicago. Amble around this family-friendly area's Chinatown and enjoy its top-notch restaurants.

Clarke House Museum

You can spend time studying the exhibits at Clarke House Museum during your travels in Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

Chicago Arts District

You can spend time browsing the exhibits at Chicago Arts District during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

On Leong Building

You can learn about the history of Chicago with a visit to On Leong Building. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Chinese American Museum of Chicago

You can spend an afternoon studying the exhibits at Chinese American Museum of Chicago in Chicago. Amble around this family-friendly area's Chinatown and enjoy its top-notch restaurants.